crossdressingstories
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Once a year
🕑 Added 2022-10-30 03:00:02 +0000 UTCImagine me. A slim eighteen year old boy, dressed. I mean Dressed. Dressed up that is, in my sister's clothes. I felt good, very good. In fact I felt incredible. I had done this several times before when my parents had been away but never to this extent. They were away for two nights, visiting Uncle George in northern Scotland, my sister was at college and I had full access to the clothes she had left at home.
I looked at myself in the mirror, standing there wearing her school uniform. She still had it though she left school for college last year and, two years younger than her, it fitted me like a glove. I studied the reflection. The wig was mine, I had bought it for a fancy-dress party two years earlier, long shoulder-length, red hair, smooth and shiny, it felt good hanging down beside my face. Medium-size clip earrings, I know they were not supposed to be worn with the uniform but lots of the girls at school did. White blouse, tight over my 'tits', just allowing my black bra to show through but not revealing the padding inside the cups. Open at the collar with two buttons temptingly undone.
Navy skirt, actually quite tight, I was wider there than Kate. And the dress was short too on me, maybe 6" above the knee, I was taller than her. Really a bit sexy. I liked that, just a hint of me being more than a schoolgirl, the possibility of more, something alluring, something desirable. And legs. I really did think I had nice legs. I was wearing black tights, 15 denier, thick enough to cover my light leg hair but thin and smooth enough to give me a good feeling. The shoes had been a problem, Kate's feet were two sizes smaller than mine. I had bought some for myself, from a factory shop I had passed on my way home from town one day. Black and shiny, with high heels, they tightened the muscles on my calves and added to the feminine look.
Trying to look like a schoolgirl had presented a little problem regarding makeup. I liked to go 'too far' when I got dressed up but dare not on that occasion. So just a little cream over my smoothed face, a little blusher, mascara, eye-shadow, I had used eyeliner in the way my friends did at school, the girls that is, to basically outline my eyes and give me an appealing look. And nail varnish, not bright but definitely there, matching the deep pink colouring on my lips.
No handbag, not appropriate here. I slipped on Kate's school blazer and looked at myself. I felt an excited thrill between my legs, this was the most realistic as a girl / woman I had ever been.
And the decision had been made for me. I knew that, at this stage, if I could convince myself absolutely nobody would 'read' me, I was going out. Yes, out of the house. I had done that before but only about five yards out of the back door. This time it was to be more than that, very much more. I had done my prospecting.
Living where we did, on the very outskirts of the suburbs, the houses were close together. Everybody knew everybody else, neighbours and so on. But in our situation it was all one-way in one sense. We always headed down the road, the post office was in that direction, and the bus stop on the way to college, and the library and all the local shops. Or at least nearly all. I was well known there and would never have dared go that way. But the other direction was different. I could walk for about two hundred yards past houses I had never visited or at least very rarely.
And there was one shop there. A local newsagent and off-licence shop with new owners, they had only been there about two months. I had been in there once about three weeks earlier, been served by the owner, a man of maybe fifty. He didn't seem very interested in his customers, had hardly noticed me. I could do it. Walk there. Go in and buy something. And walk back. I had been dreaming of this for a few years, now I was going to do it!
I was ready. I checked the small purse in my blazer pocket, several pounds in there. Keys in pocket, yes, it would definitely NOT be a good idea to lock myself out! . Sister's old school lunch pass, I took that for some reason. I paused at the front door, took a deep breath and saw the satisfying rise and fall of my 'breasts' in the hall mirror. Opened it and went out.
At that time of year it was beginning to get dark at 8 o'clock though getting lighter by the day, I knew it would be a long time if ever before I tried anything like this in the daylight. It was cool but not cold, there was a light breeze, and no rain. I looked up and down the road from the front gate, absolutely nobody in sight, I set off up the road. The excitement of that first outing, I have never forgotten it in all these years. Walking along on heels, my breasts bouncing a little, hair swinging, my tight skirt restricting my movements to an extent, it was the most gorgeous feeling. I was confident, certainly in that light nobody was going to know my secret. I was a girl out walking, to a friend's to do homework maybe, to the shop perhaps, or heading home from school.
A car came up from behind with its lights on, my heart fluttered a little but it went straight past. Another passed me going in the other direction, maybe it had slowed a little, perhaps the driver wanted to prolong the sight of my legs, the excitement between my thighs came on again. And then about a hundred yards from my own house, I met a couple, man and woman, walking towards me. They were obviously on their way back from their shopping, small carrier bag in hand, on the same side of the road as me. As we passed I strolled confidently on, though my stomach was churning.
"Good evening" said the husband.
I just had to reply. Keeping my voice light, I hoped, I replied in the same manner and walked on, the adrenaline coursing through my veins.
I reached the little shop and was delighted there was nobody else around. I pushed the door and heard the bell. I looked across towards the small till, the man I had seen before was there, serving another guy about the same age. That was the start of my real infatuation with stockings and mini-skirts, the customer turned to walk past me out of the door, and was staring at my legs as he left. He looked me in the face and smiled. I smiled back and set off down the aisle.
I quickly collected a pack of mixed salad and a carton of milk, then headed back towards the till. The shop owner looked up and smiled at me. That was the first time I had seen that look. Not just a look of politeness or interest, more than that. It was some sort of sexual interest. He was looking at my 'breasts' rise and fall as I breathed heavily and nervously, I knew he was seeing my black bra and was dreaming about what he thought was in there. I put my purchases on the counter and took my purse out. I looked past him at the display behind his head.
I smiled at him, a long wide alluring smile, I could imagine the shape of my shiny red lips.
"And a small bottle of Gordon's please."
I had often fantasised about being in a bar, showing off and with a drink in my hand. I had never ever tasted it and I rather fancied the thought of a gin and tonic.
He smiled at me, in fact no, he leered at me. OK I was a schoolgirl but an older one, a sixth former maybe, classic 'porn' - matter, exactly the age many men like to look at in the magazines.
"How old are you, dear?" he asked.
The leer appeared again.
"Eighteen" I said quietly but, I hoped, confidently.
I knew I looked older than that really, my make-up skills were sufficiently advanced by then. But I am glad he didn't ask for ID, OK I was eighteen but all my cards had the wrong sex on them.
"OK" he said and handed over the bottle.
I put a note on the counter and, before I could move, his hand went over mine. I was scared, terrified, excited, thrilled, all of these. A man was touching me, a hint of a sexual thrill went through me. He really did think I was a girl! I left my hand there for just a little too long, he increased the pressure of his hand on mine.
I escaped. Just at that moment another customer came in, the owner quickly finished serving me and turned his attention to the other customer who was just after cigarettes.
When I got outside the door I breathed deeply again. What a buzz, I was excited, this was so much fun. I walked home, two more cars passed me but all they saw was a young woman bouncing along, happy in her sexuality.
The next day I woke up thinking about what had happened. I had to do it again. Mum and Dad would be back tomorrow, today was the one chance. What should I do? Go into town, dare I go on a bus? No way! But I could go to that shop again, maybe later this time, not so many people around. I knew he shut at ten, I could maybe get there at ten minutes to, try to time it right. Yes! I spent the day going through my mother's wardrobe and drawers, and Kate's. By eight o'clock I had it all assembled, an outfit I would love to wear, and would totally adore being seen in.
I ran the water in the bath and soaked for over half an hour. My thoughts were erotic as I soaped my body and shaved my legs and then trimmed around my penis, leaving a heart shaped patch of pubic hair. I would have to hide that for a while but I thought it looked good. Then I removed all of the growth under my arms. I towelled myself dry and found my body was silky smooth. The sculptured patch of dark hair between my legs was like a target. I reached down behind my legs and pulled my penis back through my legs, the effect in the mirror was remarkable and everything I could have wished for. Where once my cock protruded there now was the appearance of a female vagina.
I began putting on the first piece of lingerie. I reached behind my back to fasten the black silk uplift-bra closely against my body, slipping two pairs of rolled-up flesh coloured tights into the lower part of the cups and doing a good job on pulling up the flesh to give an impression of breasts. When the soft, shiny fabric of the matching black panties slid across my bare thighs, 'Bethany' had taken control. It was a transformation that had occurred several times before, but it still thrilled me.
I stood in front of the bathroom mirror and began the long process of making up my face. I was confident in my skilled use of powder, blush, eye-liner, eye-shadow and lipstick. I wanted to turn myself into a sensuous woman, maybe one who could turn eyes and excite pulses. I knew just how young girls like me liked to look, and went at it just a little heavily with dark eyeliner and heavy mascara. Then I stuck on firmly a set of longish bright red nails to give my hand a definitely feminine appearance and slid four rings into place, though not on the left 'ring finger'.
Finished with the makeup, I slipped on a shoulder length wig. I avoided looking at myself critically until I had brushed and shaped my hair. Then I stepped back to see the effect.
It was a revealing moment. I had wondered why I was captivated and tormented by my desire to dress and act like a woman. Tonight was special, it was so very different from the other times. Standing in front of the mirror, I studied the woman who peered back at me in black bra and panties. I could feel myself becoming aroused by the vision of myself in the mirror and the thought that tonight that image would be part of the real world for the first time.
Glancing at the clock, I realised I had to hurry, the shop would shut in less than an hour. I sat on the bed to roll up black sheer seamed stockings and pulled them on my long legs to attach to my suspender belt. My panties clasped my penis and testicles tightly against my body. They gave me a feminine shape while hiding the exciting secret of my maleness inside the panties.
Next I stepped into my new pair of black shoes; the thin heels were nearly 5 inches high and the shoes were held by leather straps that wrapped around my ankles. I had just bought the footwear, I knew that the extra height of these shoes would be a challenge. But once I looked in the mirror and saw what the high heels did to my legs, I knew I just had to wear them for my first proper 'coming-out' appearance.
I was proud of my long, shapely legs. Tonight I was going to wear a very short black dress, dramatically tight around the waist and showing my slim figure to its best advantage.
After I zipped Kate's favourite party dress up at the back, I turned to see my reflection in the mirror. The image took my breath away. I had seen myself dressed and made up before, but this time the sheer glamour of my appearance had a devastating effect on me. I could feel myself grow weak in the legs and savoured the tingling sensation that gripped my groin. I grabbed one of Kate's coats I had chosen, it was gold vinyl, longer than my dress but only just. It matched the earrings and the chain round my neck, I thought the combination was knockout. Now to find out what other people thought. Maybe.
I was never more terrified than the moment I stepped out of the front door that evening and turned to face the world. I had the necessities, purse with money, keys, cigarettes and a cheap gold lighter, makeup items, everything a girl might need. I set off down the street. This time I met no-one until I arrived just outside the shop. As I approached from about 20 yards two young men came out and began to walk my way. As they passed I could feel the tension, they had obviously seen me. And they didn't 'read' me at all! They both smiled widely, they liked what they saw. Behind me, from about ten yards, I heard my very first wolf whistle!
I went into the shop again, this time I knew what to expect - to some extent. I had just checked the time on my mother's second best gold (plated) watch. I was late, it was very nearly ten o'clock. As I went in I could see the owner leave the counter and set off towards the door. He was going to close the shop!
"I am just closing, darling, but I'll serve you first of course."
'Darling!' he said 'darling!'
As he reached towards the door he turned the card round. It now said 'OPEN' - it must be 'CLOSED' on the other side. He came back to the counter and looked closely at me.
"Oh. Hello, I didn't recognise you," he said.
Help! Was I discovered? How?
"You were in last night weren't you? What can I do for you?"
And he said that in a sort-of mock sexy way, having a joke with a customer. I smiled widely at him and asked for a pack of cigarettes, a brand of very long thin cigarettes I imagined a girl like me would like. He got them and put them on the counter. Again, just like the previous night, he made sure he achieved bodily contact as he took the note from my fingers. And again when he gave me my change. I slipped the coins in my purse and headed for the door. He rushed to be there before me, making sure he was partly in the way. I would have to push past him to get out.
But I had other plans. I had not been sure how to do this, but the two young men had given me a chance.
"Look, I'm sorry," I stammered, "I hope you don't mind but can I wait a couple of minutes? Those two men who just left, they wolf-whistled at me, I'm a bit scared to leave right now. Could I wait here please?"
I needed to do that I needed to extend the duration of my 'being' a woman. Maybe I could just hand around for two or three minutes before going home, before having to become 'Benjamin' again.
The request somewhat floored him. I didn't think he would mind me staying but he was surprised I had actually volunteered.
"Well I am not surprised they whistled at such an attractive woman. Sure you can stay but I have to shut up the shop. How about coming through into the back?"
That I had not expected. He opened a door behind the counter to let me through into a small sitting room. I went in, hesitant but excited. He left me briefly to lock the main door - it was that which worried me, I couldn't get out. But the thrill overcame the worry.
I sat at a small table on a highish chair. As I did so I automatically crossed my legs and was rewarded with the double thrill - the sensuous feeling as my stocking-clad legs slid smoothly across each other, and the delight as my coat opened to reveal my legs, in that extremely short skirt, the hem rose to reveal my thighs.
He noticed too!
"Don't worry, you will be all right here. Can I get you a drink maybe?"
"Er - thank you," I smiled.
"A gin and tonic?"
I had drunk one, my first, at home in the living room the previous night. I liked it. OK, I shouldn't, but what else should I not be doing? Sitting there looking like that, that's for sure.
He got me a drink from the small cabinet in the corner. I took it and sipped, then asked "Do you mind if I have a cigarette?"
"No problem," he said, obviously pleased that I had to an extent settled.
I opened the pack carefully with my long nails and lit the long thin cigarette, relaxing just a little.
I sipped my drink again.
"We should introduce ourselves maybe, I'm David. Look, if you like I could give you a lift, we could avoid those guys for sure."
Was he fishing, trying to find where I lived? Surely not, he was older than my father. But then his whole body language suggested he was 'interested' in me.
"I'm Bethany," I replied, "you have not been here long have you? Do you run the shop alone, or - er - with your wife maybe?"
My tone made it obvious, I WAS fishing. He leapt in.
"On my own, I got divorced a year ago, decided on a new start here. Came from the North, this seemed a likely area. What about you. Still at school?"
My next action decided my fate for the evening. I decided to go 'on the attack'. I stood up to put out my cigarette and took my drink over to sit beside him on the couch. I sat very close, my thigh touching his. I turned to face him, and leaned over very close. I changed my voice a little, aiming for a lower, husky, sexier sound.
"Yes, still at school. Is it that obvious? Do I seem like a schoolgirl to you?"
He was interested, definitely, but embarrassed.
"Well, you look very grown up tonight. It's just the uniform. Last night, I remembered. But you look very different tonight."
"How do I look different?" I teased, leaning closer and looking in his eyes.
To be honest he wasn't a very attractive man but he was all I had, I just had to make the most of the opportunity. I put a hand on his knee, slid it upwards, towards his crotch.
I didn't give him the chance to reply, it was now or never!
"Tell me, David, do you find me attractive?"
He was flustered, surprised, he stammered a little.
"I definitely do, Bethany, I find you incredibly attractive."
He had to say that, didn't he? I was sitting there, obviously coming on to him, my right hand just touched his swollen cock under his trousers, my face was only inches from his. He just had to stare into my eyes, to look at the overdone provocative makeup, the long thick lashes, the full shiny lips. I smiled a little, put out my tongue to temptingly tease him, stroking it round to moisten my mouth ready for him. My red-tipped hand lightly touched his cock.
"David," I murmured in his ear. "I want you, now, and I can feel you want me too."
My lips played with his ear, my tongue began to probe its inner surface. I moved further toward him and pressed myself against him. My lips very gently touched his mouth, then his arms pulled me heavily against his body. He grasped my gold vinyl coat and slowly ran his hands down its slippery front, his fingers pressing on my curvaceous of my body. Then he drew it back and revealed my short minidress.
I dropped the coat to the floor. Again he pulled me to him. This time more roughly, more demanding, more assured of what he wanted. Our lips and tongues met each other, damp and wet. We pressed together and then parted, needing air, and then we returned to the sensual battle. My long fingers were feverishly exploring all parts of his body, he was caressing my satin covered buttocks, stroking my nylon stocking-clad legs. I pulled back from him. My hands ran across the front of my dress as though trying to smooth out the silky material. But instead I stood up and reached behind to unzip it, letting it slowly slide down my body, revealing first the gleam of my black satin bra, then the dark shiny panties and finally the gartered ebony stockings. I tossed the dress aside with a flick of my ultra-high-heeled foot and stood, arms akimbo, looking at the dazed shop owner.
